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Usage

Uses

Used in Pharmaceutical Industry:
S-3,3'-bis(4-nitrophenyl)-1,1'-Binaphthalene]-2,2'-diol is used as a chiral ligand for the synthesis of various chiral compounds in the pharmaceutical industry. Its ability to induce enantioselectivity in chemical reactions aids in the production of enantiomerically pure drugs, which is crucial for ensuring the desired therapeutic effects and minimizing potential side effects.
Used in Agrochemical Industry:
In the agrochemical industry, S-3,3'-bis(4-nitrophenyl)-1,1'-Binaphthalene]-2,2'-diol is employed as a chiral auxiliary for the synthesis of enantiomerically pure agrochemicals. This ensures that the active ingredients in these products are effective and have minimal impact on non-target organisms, thus promoting sustainable agriculture.
Used in Production of Fine Chemicals:
S-3,3'-bis(4-nitrophenyl)-1,1'-Binaphthalene]-2,2'-diol is utilized as a chiral ligand in the synthesis of fine chemicals, which are high-purity chemicals used in various applications such as fragrances, flavors, and specialty materials. Its enantioselective properties enable the production of high-quality enantiomerically pure fine chemicals, enhancing their performance and reducing potential side effects.

Upstream product

• 586-78-7 para-nitrophenyl bromide 
• 173831-50-0 rac-2,2'-bis-(methoxymethoxy)-1,1'-binaphthalene 
• 602-09-5 1,1'-bi-2-naphthol 
• 75714-60-2 (S)-3-bromo-1-(3-bromo-2-methoxynaphthalen-1-yl)-2-methoxynaphthalene 
• 75640-87-8 (S)-2,2'-dimethoxy-1,1'-dinaphthyl 
• 18531-94-7 (R)-1,1'-Bi-2-naphthol 

Relevant academic research and scientific papers

Photocatalyzed E→Z Contra-thermodynamic Isomerization of Vinyl Boronates with Binaphthol

The photocatalytic contra-thermodynamic E→Z isomerization of vinyl boronates by using a binaphthol catalyst is disclosed. The reaction, based on the transient formation of a suitable chromophore with a BINOL derivative as the catalyst, allowed geometrical isomerization in good-to-excellent Z/E ratio and excellent-to-quantitative yields. The mechanism of this E→Z contra-thermodynamic isomerization was studied, and the formation of a transient chromophore species is suggested.

Synthesis of Chiral 3,3?-Disubstituted (S)-BINOL Derivatives via the Kumada and Suzuki Coupling and Their Antibacterial Activity

Abstract: A new series of 3,3?-disubstituted chiral (S)-BINOL derivatives 6a–6k has been synthesized viathe Kumada and Suzuki–Miyaura coupling reactions using (S)-BINOL as the initial compound. The Kumada coupling has beenfound to be superior in terms of

Rapid synthesis of 3,3′ bis-arylated BINOL derivatives using a C-H borylation in situ suzuki-miyaura coupling sequence

The increased interest in BINOL derived catalysts for asymmetric transformations has encouraged us to disclose a rapid and scalable method of preparing 3,3′ bis-arylated BINOL derivatives 1 using a one-pot CH borylation/Suzuki-Miyaura coupling sequence. T

Diastereomeric resolution of rac -1,1′-bi-2-naphthol boronic acid with a chiral boron ligand and its application to simultaneous synthesis of (R)- and (S)-3,3′-disubstituted 1,1′-bi-2-naphthol derivatives

A new concept of diastereomeric resolution has been developed where a boronic acid functionality was employed as (1) a diastereomeric resolving group with a chiral boron ligand and (2) a masked functional group for further transformation thereafter. This new diastereomeric resolution method was successfully applied to the preparation of both (R)- and (S)-3,3′- disubstituted 1,1′-bi-2-naphthol (BINOL) derivatives in a step-ecomonical manner. Racemic BINOL boronic acid reacted with a commercially available pinene-derived iminodiacetic acid as a chiral boron ligand to generate the two diastereomers in quantitative yields over a gram-scale quantity. After the removal of the chiral boron ligand from the diastereomers under mild conditions, the subsequent Suzuki coupling reaction of the resulting chiral BINOL boronic acids with aryl halides provided a series of both (R)- and (S)-BINOL derivatives in good yields. Further, both resulting diastereomers could be directly applied to the Suzuki coupling reaction without the removal of the chiral ligand.

Chiral Bronsted acid catalyzed enantioselective Mannich-type reaction

Mannich-type reaction of ketene silyl acetals with aldimines proceeded catalytically by means of a phosphoric acid diester, derived from (R)-BINOL, as a chiral Bronsted acid to afford β-amino esters with good diastereoselectivity in favor of the syn isomer and high enantioselectivity (up to 96% ee). The highest enantioselectivity was achieved by the phosphoric acid diester bearing 4-nitrophenyl groups on the 3,3′-positions of BINOL. The N-2-hydroxyphenyl group of aldimine was found to be essential for the present Mannich-type reaction. In combination with these experimental investigations, two possible monocoordination and dicoordination pathways were explored using density functional theory calculations (BHandHLYP/6-31G*). The present reaction proceeds via a dicoordination pathway through the zwitterionic and nine-membered cyclic transition state (TS) consisting of the aldimine and the phosphoric acid. The re-facial selectivity was also well-rationalized theoretically. The nine-membered cyclic structure and aromatic stacking interaction between the 4-nitrophenyl group and N-aryl group would fix the geometry of aldimine on the transition state, and the si-facial attacking TS is less favored by the steric hindrance of the 3,3′-aryl substituents.

ASYMMETRIC-SYNTHESIS CATALYST BASED ON CHIRAL BROENSTED ACID AND METHOD OF ASYMMETRIC SYNTHESIS WITH THE CATALYST

A compound usable as an asymmetric synthesis catalyst which can be easily synthesized without using any metal such as a lanthanoid group element; a method of asymmetric synthesis with the compound; and a chiral compound obtained by the asymmetric synthesis method. A Broensted acid is used as a catalyst in asymmetric synthesis, the chiral Broensted acid being represented by formula (1) below or formula (3) below. The asymmetric synthesis method employs the catalyst. Asymmetric synthesis with the catalyst gives a chiral compound.